(3E)-6-chloro-3-{hydroxy[(pyridin-2-yl)amino]methylidene}-2-methyl-2H,3H,4H-1$l^{6},5,2-thieno[2,3-e][1$l^{6},2]thiazine-1,1,4-trione

• ChemBase ID: 4456
• Molecular Formular: C13H10ClN3O4S2
• Molecular Mass: 371.8192
• Monoisotopic Mass: 370.9801255
• SMILES: Clc1sc2c(S(=O)(=O)N(/C(=C(/O)\Nc3ncccc3)/C2=O)C)c1
• Canonical SMILES: Clc1sc2c(c1)S(=O)(=O)N(/C(=C(\Nc1ccccn1)/O)/C2=O)C
• InChI: InChI=1S/C13H10ClN3O4S2/c1-17-10(13(19)16-9-4-2-3-5-15-9)11(18)12-7(23(17,20)21)6-8(14)22-12/h2-6,19H,1H3,(H,15,16)/b13-10+
• InChIKey: OXROWJKCGCOJDO-JLHYYAGUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3E)-6-chloro-3-{hydroxy[(pyridin-2-yl)amino]methylidene}-2-methyl-2H,3H,4H-1$l^{6},5,2-thieno[2,3-e][1$l^{6},2]thiazine-1,1,4-trione
• IUPAC Traditional name: (3E)-6-chloro-3-[hydroxy(pyridin-2-ylamino)methylidene]-2-methyl-1$l^{6},5,2-thieno[2,3-e][1$l^{6},2]thiazine-1,1,4-trione
• Brand Name: Lorcam; Xafon
• Synonyms: chlortenoxicam; Acabel; CLTX; CTX; Lorcam; Lorcam (TN); Lornoxicamum; Lornoxicamum [inn-latin]; Safem; Taigalor; Telos; XEFO; Xefocam; Lornoxicam

Database IDs

• CAS Number: 70374-39-9
• PubChem SID: 160967888; 99443271
• PubChem CID: 54690031; 5282204

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.8801155
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.89714
• LogD (pH = 7.4): 1.350553
• Log P: 1.9918677
• Molar Refractivity: 97.0238 cm^3
• Polarizability: 33.356422 Å^3
• Polar Surface Area: 99.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.53
• LOG S: -3.91
• Solubility (Water): 4.61e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.62 [BIOBYTE STARLIST (2009)]

DETAILS

DrugBank - DB06725

• Drug Groups: approved
• Description: Lornoxicam (chlortenoxicam) is a new nonsteroidal anti-inflammatory drug (NSAID) of the oxicam class with analgesic, anti-inflammatory and antipyretic properties. Lornoxicam differs from other oxicam compounds in its potent inhibition of prostaglandin biosynthesis, a property that explains the particularly pronounced efficacy of the drug. Lornoxicam is approved for use in Japan.
• Indication: For the treatment of acute mild to moderate pain, as well as pain and inflammation of the joints caused by certain types of rheumatic diseases.
• Pharmacology: Lornoxicam is a non-steroidal anti-inflammatory drug (NSAID) that belongs to the oxicam class. As with other NSAIDS, lornoxicam is a potent inhibitor of the cyclooxgenase enzymes, which are responsible for catalyzing the formation of prostaglandins (act as messenger molecules in the process of inflammation) and thromboxane from arachidonic acid. Unlike some NSAIDS, lornoxicam's inhibition of cyclooxygenase does not lead to an increase in leukotriene formation, meaning that arachidonic acid is not moved to the 5-lipoxygenase cascade, resulting in the minimization of the risk of adverse events.
• Affected Organisms: Humans and other mammals
• Biotransformation: Lornoxicam is metabolized completely by cyp 2C9 with the principal metabolite being 5'-hydroxy-lornoxicam and only negligible amounts of intact lornoxicam are excreted unchanged in the urine. Approximately 2/3 of the drug is eliminated via the liver and 1/3 via the kidneys in the active form.
• Absorption: Lornoxicam is absorbed rapidly and almost completely from the GI tract (90-100%).
• Half Life: 3-5 hours
• Protein Binding: Lornoxicam is 99% bound to plasma proteins (almost exlusively to serum albumin).
• References: Balfour JA, Fitton A, Barradell LB: Lornoxicam. A review of its pharmacology and therapeutic potential in the management of painful and inflammatory conditions. Drugs. 1996 Apr;51(4):639-57. [Pubmed] ; Vane JR: Introduction: mechanism of action of NSAIDs. Br J Rheumatol. 1996 Apr;35 Suppl 1:1-3. [Pubmed] ; Radhofer-Welte S, Rabasseda X: Lornoxicam, a new potent NSAID with an improved tolerability profile. Drugs Today (Barc). 2000 Jan;36(1):55-76. [Pubmed] ; Skjodt NM, Davies NM: Clinical pharmacokinetics of lornoxicam. A short half-life oxicam. Clin Pharmacokinet. 1998 Jun;34(6):421-8. [Pubmed] ; Olkkola KT, Brunetto AV, Mattila MJ: Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents. Clin Pharmacokinet. 1994 Feb;26(2):107-20. [Pubmed] ; Hitzenberger G, Radhofer-Welte S, Takacs F, Rosenow D: Pharmacokinetics of lornoxicam in man. Postgrad Med J. 1990;66 Suppl 4:S22-7. [Pubmed] ; Pruss TP, Stroissnig H, Radhofer-Welte S, Wendtlandt W, Mehdi N, Takacs F, Fellier H: Overview of the pharmacological properties, pharmacokinetics and animal safety assessment of lornoxicam. Postgrad Med J. 1990;66 Suppl 4:S18-21. [Pubmed] ; Bonnabry P, Leemann T, Dayer P: Role of human liver microsomal CYP2C9 in the biotransformation of lornoxicam. Eur J Clin Pharmacol. 1996;49(4):305-8. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Olkkola KT, Brunetto AV, Mattila MJ: Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents. Clin Pharmacokinet. 1994 Feb;26(2):107-20. Pubmed
• Hitzenberger G, Radhofer-Welte S, Takacs F, Rosenow D: Pharmacokinetics of lornoxicam in man. Postgrad Med J. 1990;66 Suppl 4:S22-7. Pubmed
• Pruss TP, Stroissnig H, Radhofer-Welte S, Wendtlandt W, Mehdi N, Takacs F, Fellier H: Overview of the pharmacological properties, pharmacokinetics and animal safety assessment of lornoxicam. Postgrad Med J. 1990;66 Suppl 4:S18-21. Pubmed
• Bonnabry P, Leemann T, Dayer P: Role of human liver microsomal CYP2C9 in the biotransformation of lornoxicam. Eur J Clin Pharmacol. 1996;49(4):305-8. Pubmed
• Balfour JA, Fitton A, Barradell LB: Lornoxicam. A review of its pharmacology and therapeutic potential in the management of painful and inflammatory conditions. Drugs. 1996 Apr;51(4):639-57. Pubmed
• Radhofer-Welte S, Rabasseda X: Lornoxicam, a new potent NSAID with an improved tolerability profile. Drugs Today (Barc). 2000 Jan;36(1):55-76. Pubmed
• Skjodt NM, Davies NM: Clinical pharmacokinetics of lornoxicam. A short half-life oxicam. Clin Pharmacokinet. 1998 Jun;34(6):421-8. Pubmed
• Vane JR: Introduction: mechanism of action of NSAIDs. Br J Rheumatol. 1996 Apr;35 Suppl 1:1-3. Pubmed